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Potassium Carbonate → [3-[2-[1-(6-Chlorobenzothiazole-2-yl)pyrrolidine-3-ylamino]ethoxy]phenyl]acetic acid methyl ester

HRID 420595
Notes
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Reaction equation

HRID 420595 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([N:9]3[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:17][O:18][C:19](=[O:31])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29]Br)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:17][O:18][C:19](=[O:31])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][NH:14][CH:11]2[CH2:12][CH2:13][N:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([Cl:1])[CH:16]=[CH:15][C:5]=4[N:6]=3)[CH2:10]2)[CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 579660771-(6-Chlorobenzothiazole-2-yl)pyrrolidine-3-ylamineHCID 66657854Methyl[3-(2-bromoethoxy)phenyl]acetate

Product 1

HCID 57966337[3-[2-[1-(6-Chlorobenzothiazole-2-yl)pyrrolidine-3-ylamino]ethoxy]phenyl]acetic acid methyl esterYield 52.1%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(6-chlorobenzothiazole-2-yl)pyrrolidine-3-ylamine (190 mg), [3-(2-bromoethoxy)phenyl]acetic acid methyl ester (205 mg) and potassium carbonate (114 mg) was stirred at 80° C. for 2 hours. To the reaction solution, was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (174 mg). Yield: 52%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-1013c5b79c77404f987c34223a26b60d
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08097610B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes